Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (3,5-Difluorophenyl)boronic acid | HCID 2734338 | — |
| Reactant | Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate | HCID 25067323 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59560293 | HCID 59560293 | 26.6% |
Reaction Steps
A mixture of 4-hydroxy-2,2-dimethyl-2,3-dihydrobenzofuran-6-carboxy-lic acid methyl ester (3e) (1 g, 0.0045 mol), 3,5-difluorophenylboronic acid (1.07 g, 0.0068 mol), Cu(OAc)2 (0.9 g, 0.005 mol), freshly activated 4 Å molecular sieves (4 g) and Et3N (4 mL) in CH2Cl2 (25 mL) was stirred at room temperature under N2 for 48 hrs. The mixture was filtered through Celite and the filter cake was washed with CH2Cl2. The filtrate was concentrated to give a dark liquid. The crude liquid was purified by column chromatography eluting with EtOAc/petroleum ether (1/5) to give the title compound (0.4 g, 26.6%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.18 (s, 1H), δ 7.14 (s, 1H), 6.47(m, 1H), δ 6.36 (dd, 2H), 3.81 (s, 3H), 2.83 (s, 2H), 1.41 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08119624B2 |
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| Source dataset | uspto-grants-2012_02 |
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| ORD ID | ord-5f6f025061954c05aa2521eaae619775 |
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| Source note | uspto-grants-2012_02 |
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